Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Chilmark vacation rentals

Private beach nearby, beach bar

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (346 reviews)
"The place was excellent"
United States
Delia
The price is ￥25,886
￥29,628 total
includes taxes & fees
Jan 29 - Jan 30
The Club at New Seabury
On the beach, white sand

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (197 reviews)
"This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!"
United States
Jeff
The price is ￥20,506
￥23,469 total
includes taxes & fees
Jan 21 - Jan 22
InnSeason Resorts Captain's Quarters
Beach nearby

Near Old Silver Beach Falmouth- Two bedroom , private bathroom and kitchenette.

Near Old Silver Beach Falmouth- Two bedroom , private bathroom and kitchenette.
Falmouth
8.2 out of 10, Very Good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is ￥15,496
￥31,670 total
includes taxes & fees
Jan 21 - Jan 22
Near Old Silver Beach Falmouth- Two bedroom , private bathroom and kitchenette.
Interior

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "
United States
ralpjh c.
The price is ￥39,152
￥68,824 total
includes taxes & fees
Feb 1 - Feb 2
Charming cottage overlooking the bay in Padanaram Village.
Exterior

Falmouth Oasis

Falmouth Oasis
2.0 star property
Falmouth
The price is ￥22,769
￥68,768 total
includes taxes & fees
Jan 25 - Jan 26
Falmouth Oasis
Interior

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (212 reviews)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is ￥25,615
￥78,179 total
includes taxes & fees
Jan 25 - Jan 26
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Smart TV, DVD player

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (24 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is ￥49,830
￥104,077 total
includes taxes & fees
Jan 21 - Jan 22
The Seashell Cove - Martha's Vineyard
Terrace/patio

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"perfect for our needs"
United States
Ed V.
The price is ￥47,436
￥105,797 total
includes taxes & fees
Feb 20 - Feb 21
Oak Bluffs - Quiet neighborhood
Terrace/patio

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is ￥45,559
￥111,888 total
includes taxes & fees
Jan 21 - Jan 22
Spring Escape in Hatchville – Sleeps 6 + Dogs!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (3 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is ￥55,342
￥141,296 total
includes taxes & fees
Jan 30 - Jan 31
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Outdoor dining

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Aaron Q.
The price is ￥99,473
￥181,169 total
includes taxes & fees
Feb 2 - Feb 3
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Interior

Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!
2.5 star property
Falmouth
The price is ￥96,058
￥229,018 total
includes taxes & fees
Jan 22 - Jan 23
Cape Cod Escape at Casa de Leo!
Smart TV, books

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Dartmouth
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is ￥86,966
￥191,634 total
includes taxes & fees
Jan 30 - Jan 31
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Terrace/patio

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"The hosts are excellent people, great communicators who want VBRO guests to have an outstanding experience. Chappy is a wonderful retreat from the rest of the world. That is my only word of caution, it requires a ferry to eat out or shop. Otherwise this is a great place to read write meditate beach and let go of everyday worries. It has a higher price tag because your paying for a premium location, guest service experience and higher quality accomodation."
United States
SparkleCappy
The price is ￥111,712
￥167,878 total
includes taxes & fees
Feb 1 - Feb 2
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Exterior

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is ￥79,060
￥171,499 total
includes taxes & fees
Jan 21 - Jan 22
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Exterior

The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft
Mattapoisett
9.8 out of 10, Exceptional, (8 reviews)
"Great stay! Great property!"
United States
Liz A.
The price is ￥103,126
￥275,303 total
includes taxes & fees
Feb 11 - Feb 12
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Smart TV

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (88 reviews)
"Very happy. Thank you for the stay."
United States
Gillian S.
The price is ￥64,039
￥104,738 total
includes taxes & fees
Jan 25 - Jan 26
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs
9.4 out of 10, Exceptional, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is ￥60,481
￥100,232 total
includes taxes & fees
Jan 25 - Jan 26
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chilmark Hotel Reviews

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Spotless, beautiful room with comfortable bed, and welcoming staff through the inn. Also, very close to the ferry and shops/restaurants; ideal location. Would definitely stay here again (and again)!"
Catherine 2-night trip
Posted 2 days ago
Mansion House Inn And Spa

Find out more about Chilmark

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Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best vacation rentals that Chilmark has to offer?

9-bedroom vacation home near Cape Cod Beaches: This vacation home rental near Chilmark is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chilmark?

Choose from 75 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Squibnocket Pond are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.